US2916369A

US2916369A - Diallylthiolcarbamates and their use as herbicides

Info

Publication number: US2916369A
Application number: US612115A
Authority: US
Inventors: Tilles Harry; Antognini Joe
Original assignee: Stauffer Chemical Co
Current assignee: Stauffer Chemical Co
Priority date: 1956-09-26
Filing date: 1956-09-26
Publication date: 1959-12-08
Anticipated expiration: 1976-12-08

Description

United States Patent DIALLYLTHIOLCARBAMATES AND THEIR USE AS HERBICIDES 1 No Drawing. Application September 26, 1956 Serial No. 612,115

10 Claims. (Cl. 71-2.7)

This invention relates to certain novel diallyl thiolcarbamates as compositions of matter and as herbicides. More specifically, the invention relates to compounds of the general formula 0 nsi lNwEzcHzonm wherein R is a lower alkyl radical. The novel compounds of the present invention may be made in accordance with the following non-limiting examples. Code numbers have been assigned to each compound and are used throughout the balance of the application.

Example 1--(R-2007).-About 33.4 g. (0.337 mole) of di-allylamine was dissolved in 200 cc. of benzene and solution was cooled to C. To this mixture was then added with stirring a solution of 20 g. (0.161 mole) of ethyl chlorothiolformate in 30 cc. of benzene over an interval of 24 minutes at 5-13 C. with ice cooling. The ice bath was then removed and the mixture was stirred for an additional 20 minutes. It was then filtered and the cake was washed with 2-50 cc. portions of benzene.

F 2,916,369 Patented Dec. 8, 1959 of diallylamine and 11 g. (0.072 mole) of n-butyl chlorothiolformate were employed, there was obtained 12.98 g. (84.4% yield) of n-butyl N,N-diallylthiolcarbamate, B.P. mm.) 136.5138.0 C.

The compounds of the present invention have been tested as herbicides and found very effective as the following typical tests show. Some of the compounds are quite selective in their action and can be used to eradicate or control one type of plant, while another type of plant is relatively unaffected.

In making the following tests, seeds were planted in 3" pots and shortly thereafter the compound under test was applied to the pots as a drench at the rate of 365 pounds per acre. The pots were placed in a greenhouse and watered at suitable intervals and the germination and growth of the seeds was compared with similarly planted seeds to which no herbicide was added. In each case, germination was reported on the scale of 0100%, while growth was reported on a scale of 0-10, based on the seeds which germinated. Thus, 100-10 indicates normal germination and normal growth.

The following data were obtained:

Cucumbers Radish Oats Compound Percent Growth Percent Growth Percent Growth Germ. Germ R-20l6 0 R20l8 0 Pea Corn Radish Rye Lbs. Cucumber Compound Rate] Acre Germ Gr Germ. Gr. Germ. Gr. Germ. Gr.

10 100 4 100 10 100 10 a a i 32. a a it a .2 a; 2 as i8 4o 10 1 100 7 100 10 The filtrate was evaporated on a steam bath and the residual liquid was fractionally distilled. There was obtained 24.77 g. (83.2% yield) of ethyl N,N-diallylthiolcarbamate, B.P. (30 mm.) 133-136.5 C.

Example 2-(R-2016).-About 15.0 g. (0.152 mole) of di-allylamine was dissolved in 100 cc. of ethyl ether and the solution was cooled to 5 C. To this mixture was then added dropwise a solution of 10 g. of n-propylchlorothiolformate in 20 cc. of ethyl ether. The mixture was filtered and the cake was washed with a small amount of ethyl ether. The filtrate was evaporated on a steam bath and the residual liquid was then fractionally distilled. There was obtained 11.02 g. (76.5% yield) of n-propyl N,N-diallylthiolcarbamate, B.P. (15 mm.) 132.0-132.2 C. The following analysis was obtained:

Example 3-(R-2018).-When the general procedure of Example 2 was repeated except that 15 g. (0.152 mole) The compounds of the present invention may be used as preemergence or postemergence herbicides and may be applied in a variety of ways at various concentrations. They may be combined with suitable carriers and applied as dusts, sprays or drenches. The amount applied will depend on the nature of the seeds or plants to be controlled and the rate of application may vary from 1 to 500 pounds per acre. One particularly advantageous way of applying the compounds is as a narrow band along a row crop, straddling the row.

We claim:

1. The method of combatting weeds comprising applying a phytotoxic amount of a compound to the soil, said compound having the formula H RSCN(CH2CE: CH2):

v 2,916,369 a u 3 4 6. The method of claim 1 wherein the compound is References Cited in the file of this patent n-butyl N,N-diallylthiolcarbamate. UNITED STATES PATENTS t 7 As a new mmposmon of mat er 2,060,733 Hunt et a1 Nov. 10, 1936 H 5 2,160,880 Loane et al June 6, 1939 2,562,011 Baumgartner July 24, 1951 2,642,451 Weijlard et al June 16, 1953 wherein R is a lower alkyl radical. 2,650,876 Stewart Sept. 1, 1953 8. As a new composition of matter ethyl N,N-dial1y1- 2,687,348 Kosmin Aug. 24, 1954 thiolcarbamate.

9. As a new composition of matter n-propyl N,N- 10 OTHER REFERENCES diallylthiolcarbamate. Chemical Abstracts, vol. 5, 1911, pps. 1095 and 1096. 10. As a new composition of matter n-butyl N,N- Riemschneider et al.: Monatschefte fur Chemie 84, diallylthiolcarbamate. 518-21 (1953).

Claims

1. THE METHOD OF COMBATTING WEEDS COMPRISING APPLYING A PHYTOTOXIC AMOUNT OF A COMPOUND TO THE SOIL, SAID COMPOUND HAVING THE FORMULA

7. AS A NEW COMPOSITION OF MATTER